Dichloromethane → HCID 89656105, compound

HRID 930956Notes

Reaction equation

HRID 930956 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.[Br:7][C:8]1[CH:9]=[C:10]([S:15]([N:18]2[CH2:23][CH2:22][CH:21]([OH:24])[CH2:20][CH2:19]2)(=[O:17])=[O:16])[CH:11]=[CH:12][C:13]=1[F:14].O.CC1C=CC(S(O)(=O)=O)=CC=1.ClCCl>O>[Br:7][C:8]1[CH:9]=[C:10]([S:15]([N:18]2[CH2:19][CH2:20][CH:21]([O:24][CH:6]3[CH2:5][CH2:4][CH2:3][CH2:2][O:1]3)[CH2:22][CH2:23]2)(=[O:17])=[O:16])[CH:11]=[CH:12][C:13]=1[F:14]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 80803,4-dihydro-2H-pyranHCID 521998p-Toluenesulfonic acid monohydrateHCID 89656120HCID 89656120, compound

Product 1

HCID 89656105HCID 89656105, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3,4-Dihydro-2H-pyran (0.28 mL, 3.1 mmol) was added dropwise to a 0° C. solution of Example 354a (0.51 g, 1.5 mmol), 4-methylbenzenesulfonic acid hydrate (0.59 g, 3.1 mmol), and dichloromethane (28 mL). The reaction mixture was stirred at ambient temperature for 5 hours. Water was added and the mixture was extracted with dichloromethane. The organic layer was washed with water, saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography (silica gel, dichloromethane/gradient with methanol) to afford the title compound (420 mg, 65.9% yield).

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe organic layer was washed with water, saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (silica gel, dichloromethane/gradient with methanol)

Sources & evidence

ORD record
ord-e3f0ba736eb845878cbc39b77ff3c568
Source dataset
uspto-grants-2016_03
Patent number
US09296741B2

Reaction notes

Loading…